(3-Bromopropyl)benzene → HCID 69344821, compound

Participants

Reaction Conditions

Reaction Steps

According to Scheme 22 Method A: To a solution of 5-bromo-2-methoxypyridine (1 eq, 2.70 mmol, 0.50 g) in THF (4.4 mL) at −78° C. under nitrogen was added dropwise n-butyl lithium (1 eq, 2.5M in hexanes, 2.70 mmol, 1.10 mL). The reaction mixture was stirred at −78° C. for 30 min. and 1-(3-bromopropyl)benzene (1 eq, 2.70 mmol, 0.40 mL) in solution in THF (1 mL) was added dropwise. The reaction mixture was stirred at −78° C. for 30 min. and then allowed to warm to room temperature for 1 hour. The reaction was quenched at 0° C. with water and extracted with Et2O. The organic phase was dried over Na2SO4, filtered and solvent was removed under reduced pressure leaving an orange oil. This residue was purified by flash chromatography over silicagel (AIT Flashsmart prepacked column SiO2, cyclohexane/AcOEt 97.5/2.5), yielding the title compound (0.46 mmol, 0.10 g, 17%) as a colorless semi-solid.

Provenance & Evidence